One perfect example how Rob Ford was penny rich but sense poor. Rob Ford cut much of the tree trimming budget for the city. I don't have exact quotes but I remember watching city council and he just didn't understand why trees should cost so much. It was a waste to him. Gravy. That small percentage of the cities budget was essential for him to cut because it was 'waste'. Fast forward a few months and Toronto gets hit with an ice storm (which is common in Canada after all). All of those trees which should have been trimmed and managed ended up taking out all of the powerlines in my neighbourhood. It cost Toronto hydro a small fortune (which the city covers) to get power restored and to cut back the trees which hadn't been properly maintained by the city.
So the question is did Rob Ford save the city money? He counts the small budget savings as a yes towards his mythical billion dollars of savings but the reality is that Toronto would have been far better and saved a lot more money maintaining the trees than having to pay massive amounts on OT pay to restore the damage his choices caused. The man had little foresight and acted on feelings not facts.
Generally speaking, it's hard to get people to unanimously agree to risk mitigation spending, since they don't tangibly see the benefit, which is a potential reduction in the fallout spending.